bis(2-bromophenyl)silane | 1428127-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(2-bromophenyl)silane
• 英文别名: Bis(2-bromophenyl)silane
• CAS: 1428127-13-2
• 化学式: C₁₂H₁₀Br₂Si
• 分子量: 342.105
• InChiKey: BLBBFIVRKNHOOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  48 °C
• 沸点：
  349.6±42.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  bis(2-bromophenyl)silane 在 magnesium 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以71%的产率得到9-phenyl-9,10-disilatriptycene
  参考文献：
  名称：

  微波辅助高效一锅法合成9-苯基-9,10-二硅三茂铁及其桥头官能化

  摘要：

  通过双（2-溴苯基）硅烷（1）与镁在THF中的反应合成9-苯基-9,10-二硅三茂铁（2）。在常规加热，2和顺式-9,10-二苯基-9,10-二氢-9,10- disilaanthracene（顺式- 3）在31％和36％的收率分别获得。然而，在微波辐射下，2的产率显着增加至71％。理论计算表明，从产生的中间格氏试剂反式-与顺-9,10-二芳基-9,10-二氢-9,10-二硅蒽蒽对于9,10-二硅三萜骨架的构建具有完全不同的反应性。的桥头位的Si-H部分2被容易地官能化以得到几个9,10- disilatriptycene衍生物。

  DOI：

  10.1021/om301170r
• 作为产物：
  描述：

  1,2-二溴苯 在 C₃H₇BrMg*ClLi 、 二氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以75%的产率得到bis(2-bromophenyl)silane
  参考文献：
  名称：

  具有 9,10-二硅三萜骨架的烷氧基（四芳基）硅酸盐

  摘要：

  AbstractAs anionic five‐coordinate silicon species (five‐coordinate silicates) exhibit high reactivity and unique fluxional behavior, their structure and property have received substantial attention. We report herein synthesis, structure, and fluxional behavior of alkoxy(tetraaryl)silicates having the 9,10‐disilatriptycene skeleton (6− and 7−). The molecular structure of the cryptate salt [Li(crypt‐222)]+7− shows that the five‐coordinate silicon adopts a distorted trigonal bipyramidal structure with oxygen atom occupying an equatorial position. In the 1H and 13C{1H} NMR spectra of [Li(crypt‐222)]+7−, a set of signals due to o‐phenylene blades in 7− was observed at room temperature, which indicates fluxional behavior of 7− on the NMR timescale. Computational study suggests that the observed process proceeds via a 120° rotation of bidentate ligand around the Si‐Si axis that consists of two sequential Berry pseudorotations.

  DOI：

  10.1002/hc.21481

文献信息

• Alkoxy(tetraaryl)silicates bearing 9,10-disilatriptycene skeleton
  作者：Shintaro Ishida、Minori Takiguchi、Takeaki Iwamoto

  DOI：10.1002/hc.21481

  日期：2018.12

  AbstractAs anionic five‐coordinate silicon species (five‐coordinate silicates) exhibit high reactivity and unique fluxional behavior, their structure and property have received substantial attention. We report herein synthesis, structure, and fluxional behavior of alkoxy(tetraaryl)silicates having the 9,10‐disilatriptycene skeleton (6− and 7−). The molecular structure of the cryptate salt [Li(crypt‐222)]+7− shows that the five‐coordinate silicon adopts a distorted trigonal bipyramidal structure with oxygen atom occupying an equatorial position. In the 1H and 13C1H} NMR spectra of [Li(crypt‐222)]+7−, a set of signals due to o‐phenylene blades in 7− was observed at room temperature, which indicates fluxional behavior of 7− on the NMR timescale. Computational study suggests that the observed process proceeds via a 120° rotation of bidentate ligand around the Si‐Si axis that consists of two sequential Berry pseudorotations.
• Microwave-Assisted Efficient One-Pot Synthesis of 9-Phenyl-9,10-disilatriptycene and Its Bridgehead Functionalization
  作者：Takayoshi Kuribara、Shintaro Ishida、Takako Kudo、Soichiro Kyushin

  DOI：10.1021/om301170r

  日期：2013.4.8

  9-Phenyl-9,10-disilatriptycene (2) was synthesized by the reaction of bis(2-bromophenyl)silane (1) with magnesium in THF. On conventional heating, 2 and cis-9,10-diphenyl-9,10-dihydro-9,10-disilaanthracene (cis-3) were obtained in 31% and 36% yields, respectively. However, the yield of 2 was significantly increased to 71% on microwave irradiation. Theoretical calculations suggest that the intermediary

  通过双（2-溴苯基）硅烷（1）与镁在THF中的反应合成9-苯基-9,10-二硅三茂铁（2）。在常规加热，2和顺式-9,10-二苯基-9,10-二氢-9,10- disilaanthracene（顺式- 3）在31％和36％的收率分别获得。然而，在微波辐射下，2的产率显着增加至71％。理论计算表明，从产生的中间格氏试剂反式-与顺-9,10-二芳基-9,10-二氢-9,10-二硅蒽蒽对于9,10-二硅三萜骨架的构建具有完全不同的反应性。的桥头位的Si-H部分2被容易地官能化以得到几个9,10- disilatriptycene衍生物。